Couchsurfing Chicago

During the last three days I have become a complete and utter couchsurfing convert. Couchsurfing may be the most incredible tool made available for travelers since Lonely Planet started writing guidebooks back in 1972. Let me explain.....

My host Gabriel lives in Logan Square, a few miles outside downtown Chicago. He works as an independent film maker and spent five months in Europe shooting a documentary on the Couchsurfing project. His positive experience lead to his hosting travelers when he returned to the states.

Gabriel took me to a great Mexican restaurant a few blocks from his house. The neighborhood has a strong Latino presence and the food was excellent. After dinner, we returned to the apartment and I situated myself into my new home. I would be sleeping on a futon in a corner of the apartment and Gabe provided a personal set of keys, which surprised me as I was given the freedom to come and go as I wished. It had been a long day of traveling and after a few emails and some reading, I called it a night.

The next morning I took the “L”, Chicago’s elevated train and subway, downtown. I spent a few hours exploring and taking pictures before visiting the Chicago Art Institute, home to a number of amazing pieces as well as a handful of bizarre modern works.

All the introspection and interpretation (does the subject’s red skin signify social strife in the painters society, or did he just have a sunburnt model?) left me famished and I treated myself to Chicago’s famous deep-dish pizza. I ordered the smallest pizza I could and was left utterly emasculated when I was unable to finish more than half. Now, dear reader, this isn’t your ordinary Dominos delivery - this pizza is deep (2+ inches) and contains enough fat in a single piece to power a small city for a week. In that regard, it is extremely similar to Ryan Wilson’s mother. But I digress......

After admitting defeat, I waddled slowly across town to an evening class at thinkorswim, a local brokerage that specializes in options trading. While I won’t bore non-financial geeks with the minutia, I will say that the class was extremely interesting, informative and left me with visions of grandeur concerning my future trading success.

Through the Couchsurfing network, I’d been in touch with a Chicago resident named Jared who lived downtown and was a fellow investment banker. I gave him a call and he invited me over to his apartment for drinks with himself and some friends. Jared and his friends were welcoming, extremely friendly and great company. He occupied a beautiful apartment on the 19th floor of a downtown building with stunning views. A rooftop tour revealed an even more beautiful view of Chicago. Over drinks and cigars, we talked (as business geeks are prone to do) about the economy, the future of the nation and several other matters in which we have nearly no control whatsoever. As it grew late and I faced a 45 minute walk/train ride to return to Gabriel’s place, I took Jared up on a hospitable offer and crashed on his couch.

The next day I returned to Gabriel’s place destined for the Museum of Science and Industry. I’d been to this colossal playground nearly a decade before and remembered it for it’s intriguing and interactive exhibits. The museum didn’t disappoint as both Gabriel and I spent a great afternoon viewing captured German U-boats, watching Omni Max movies and touring a simulated coal mine.

After a brief rest and burrito break, I went out for one final night in Chicago. I was headed downtown to an open floor swing-dancing evening at a local studio. As a veteran Montanan swing dancer, I was looking forward to showing off my polished moves to the slick city crowd. I arrived at the studio to find a small crowd of less than 15 due to nearly 5 inches of snow that had fallen. My visions of dancing supremacy quickly evaporated as I discovered that nearly all the dancers were far better than me. Most were well trained in traditional swing, not the country bar two step I’d learned/developed in Montana. Regardless, I had a great time dancing and talking with a number of people I met. One of the dancing attendees, a girl named Yana, happened to be a kindred Investment Banker. We struck up a great conversation and ended up talking finance for a bit over drinks before I headed back to Gabriel’s place.

The next morning was bittersweet as I departed Chicago and drove towards Pittsburgh. I’d pulled into town days earlier not knowing a soul. Since then, I’d made multiple friends, shared numerous stimulating discussions and managed to score free lodging and local information along the way! My Chicago experience was all it took to get me completely hooked on couchsurfing.

I’ll post picture of my Chicago escapades in the future as I’ve left most of my camera equipment in my car during my trek into the depths of New York. I’ll be posting both pictures and future details soon.....